Objective The effect of introducing electron-withdrawing group on the yield and isomer distribution of 2-(5-chlorobenzotriazolyl) acetonitriles were discussed. Methods 2-(5-Chlorobenzotriazolyl) acetonitriles were synthesized from 5-chlorobenzotriazole and chloroacetonitrile with anhydrous K2CO3 as the acid- binging agent in ethyl acetate. The products were characterized by IR and 1H-NMR.Results Three isomers of the title products were 2-(5-chloro-2H-benzotriazol-2-yl) acetonitrile ( C1) , 3-(5-chloro-1H-benzotriazol-1-yl) acetonitrile ( C2 ) and 2-(5-chloro-1 H-benzotriazol-1-yl ) acetonitrile ( C3 )with a yield of 21.34％, 22.47％ and 33.70％ , respectively. The total yield of 77.52％ was higher higher than that of 2-( benzotriazolyl)-acetonitriles from the reaction of benzotriazole with chloroacetonitrile (59.31％). Conclusion The number of isomers and total yield of 2-(5-Chlorobenzotriazolyl)- acetonitriles is greater than those of 2-(benzotriazolyl)acetonitriles.%目的 探讨5-氯苯并三氮唑N-上引入乙腈基所得产物异构体组成分布和产率的影响.方法 以5-氯苯并三氮唑和苯并三氮唑分别与氯乙腈反应,在无水碳酸钾/乙酸乙酯的反应体系中、100 ℃ 温度条件下合成了目标化合物,并采用红外吸收光谱,核磁共振图谱进行结构表征.结果 苯并三氮唑及衍生物与氯乙腈在无水碳酸钾作用下反应,反应物不同,目标化合物异构体为:2-乙腈基-5-氯苯并三氮唑(C1),3-乙腈基-5-氯苯并三氮唑(C2)和1-乙腈基-5-氯苯并三氮唑(C3),其组成分布和总得率都不同,其结果分别为:N-乙腈基-5-氯苯并三氮唑有三种结构异构体,总得率77.52%;N-乙腈基苯并三氮唑有两种结构异构体,总得率59.31%.结论 与苯并三氮唑相比,5-氯苯并三氮唑N-乙腈基取代得到的目标化合物异构体数目多,总产率高.
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